CA2146286A1 - Adhesifs d'hydrogel a base d'esters polyacrylate et polymethacrylate - Google Patents

Adhesifs d'hydrogel a base d'esters polyacrylate et polymethacrylate

Info

Publication number: CA2146286A1
Authority: CA; Canada
Prior art keywords: group; water soluble; hydrogel adhesive; soluble monomer; hydrogel
Prior art date: 1994-04-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002146286A

Other languages

English (en)

Inventor

Jinsong Tang

Norbert J. Mruk

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Graphic Controls Corp

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-04-06

Filing date

1995-04-04

Publication date

1995-10-07

1995-04-04 Application filed by Individual filed Critical Individual

1995-10-07 Publication of CA2146286A1 publication Critical patent/CA2146286A1/fr

Status Abandoned legal-status Critical Current

Links

230000001070 adhesive effect Effects 0.000 title claims abstract description 109
239000000853 adhesive Substances 0.000 title claims abstract description 105
239000000017 hydrogel Substances 0.000 title claims abstract description 103
150000002148 esters Chemical class 0.000 title description 8
229920000058 polyacrylate Polymers 0.000 title description 6
229920000193 polymethacrylate Polymers 0.000 title description 5
239000000178 monomer Substances 0.000 claims abstract description 92
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
-1 acrylate ester Chemical class 0.000 claims abstract description 30
229920001577 copolymer Polymers 0.000 claims abstract description 24
238000000034 method Methods 0.000 claims abstract description 20
229920000642 polymer Polymers 0.000 claims abstract description 19
230000000379 polymerizing effect Effects 0.000 claims abstract description 7
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 27
CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims description 25
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical group [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
239000003431 cross linking reagent Substances 0.000 claims description 9
229920002401 polyacrylamide Polymers 0.000 claims description 8
238000004132 cross linking Methods 0.000 claims description 7
VSFOXJWBPGONDR-UHFFFAOYSA-M potassium;3-prop-2-enoyloxypropane-1-sulfonate Chemical group [K+].[O-]S(=O)(=O)CCCOC(=O)C=C VSFOXJWBPGONDR-UHFFFAOYSA-M 0.000 claims description 7
PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 claims description 6
239000003792 electrolyte Substances 0.000 claims description 6
235000011187 glycerol Nutrition 0.000 claims description 6
PNOXUQIZPBURMT-UHFFFAOYSA-M potassium;3-(2-methylprop-2-enoyloxy)propane-1-sulfonate Chemical compound [K+].CC(=C)C(=O)OCCCS([O-])(=O)=O PNOXUQIZPBURMT-UHFFFAOYSA-M 0.000 claims description 6
238000010526 radical polymerization reaction Methods 0.000 claims description 6
RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
239000003906 humectant Substances 0.000 claims description 5
125000003010 ionic group Chemical group 0.000 claims description 5
239000001103 potassium chloride Substances 0.000 claims description 5
235000011164 potassium chloride Nutrition 0.000 claims description 5
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 4
150000003926 acrylamides Chemical class 0.000 claims description 4
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical group C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 4
229910018830 PO3H Inorganic materials 0.000 claims description 3
229910006069 SO3H Inorganic materials 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
239000004034 viscosity adjusting agent Substances 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 claims description 2
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 2
230000003472 neutralizing effect Effects 0.000 claims 2
238000003825 pressing Methods 0.000 claims 2
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 abstract 1
239000000203 mixture Substances 0.000 description 30
229920001519 homopolymer Polymers 0.000 description 19
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 16
229920003169 water-soluble polymer Polymers 0.000 description 11
239000004820 Pressure-sensitive adhesive Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000013638 trimer Substances 0.000 description 5
RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
239000003999 initiator Substances 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 3
239000000499 gel Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
229910014033 C-OH Inorganic materials 0.000 description 2
229910014570 C—OH Inorganic materials 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000002998 adhesive polymer Substances 0.000 description 2
125000002843 carboxylic acid group Chemical group 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000006071 cream Substances 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000010894 electron beam technology Methods 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000012456 homogeneous solution Substances 0.000 description 2
230000000977 initiatory effect Effects 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012544 monitoring process Methods 0.000 description 2
229920006289 polycarbonate film Polymers 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
229920000098 polyolefin Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
230000002195 synergetic effect Effects 0.000 description 2
CCTFAOUOYLVUFG-UHFFFAOYSA-N 2-(1-amino-1-imino-2-methylpropan-2-yl)azo-2-methylpropanimidamide Chemical compound NC(=N)C(C)(C)N=NC(C)(C)C(N)=N CCTFAOUOYLVUFG-UHFFFAOYSA-N 0.000 description 1
XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920000298 Cellophane Polymers 0.000 description 1
235000013175 Crataegus laevigata Nutrition 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
229920000569 Gum karaya Polymers 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
101100180320 Mus musculus Itln1 gene Proteins 0.000 description 1
101100180325 Oncorhynchus mykiss itln gene Proteins 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
241000934878 Sterculia Species 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000002313 adhesive film Substances 0.000 description 1
239000002390 adhesive tape Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
208000030961 allergic reaction Diseases 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
125000004386 diacrylate group Chemical group 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
238000013213 extrapolation Methods 0.000 description 1
230000004927 fusion Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000005865 ionizing radiation Effects 0.000 description 1
239000000231 karaya gum Substances 0.000 description 1
235000010494 karaya gum Nutrition 0.000 description 1
229940039371 karaya gum Drugs 0.000 description 1
230000007774 longterm Effects 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
230000002794 monomerizing effect Effects 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
230000007383 nerve stimulation Effects 0.000 description 1
229940065472 octyl acrylate Drugs 0.000 description 1
ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920000083 poly(allylamine) Polymers 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000037307 sensitive skin Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
238000001248 thermal gelation Methods 0.000 description 1
238000013271 transdermal drug delivery Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/58—Adhesives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0014—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Organic Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hematology (AREA)
Chemical Kinetics & Catalysis (AREA)
Adhesives Or Adhesive Processes (AREA)
Materials For Medical Uses (AREA)

CA002146286A 1994-04-06 1995-04-04 Adhesifs d'hydrogel a base d'esters polyacrylate et polymethacrylate Abandoned CA2146286A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US22355094A	1994-04-06	1994-04-06
US08/223,550		1994-04-06

Publications (1)

Publication Number	Publication Date
CA2146286A1 true CA2146286A1 (fr)	1995-10-07

Family

ID=22836987

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002146286A Abandoned CA2146286A1 (fr)	1994-04-06	1995-04-04	Adhesifs d'hydrogel a base d'esters polyacrylate et polymethacrylate

Country Status (4)

Country	Link
US (1)	US5614586A (fr)
EP (1)	EP0676457B1 (fr)
CA (1)	CA2146286A1 (fr)
DE (1)	DE69505176T2 (fr)

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US5786439A (en)	1996-10-24	1998-07-28	Minimed Inc.	Hydrophilic, swellable coatings for biosensors
AU4743696A (en) *	1995-12-29	1997-07-28	Minnesota Mining And Manufacturing Company	Use of pendant photoreactive moieties on polymer precursors to prepare hydrophilic pressure sensitive adhesives
US5868136A (en) *	1996-02-20	1999-02-09	Axelgaard Manufacturing Co. Ltd.	Medical electrode
GB9909348D0 (en) *	1998-07-31	1999-06-16	First Water Ltd	Bioadhesive compositions
GB9816826D0 (en)	1998-07-31	1998-09-30	First Water Ltd	Bioadhesive compositions
EP0836864A3 (fr)	1996-10-18	2000-03-08	Graphic Controls Corporation	Electrode de défibrillation
US6800278B1 (en)	1996-10-28	2004-10-05	Ballard Medical Products, Inc.	Inherently antimicrobial quaternary amine hydrogel wound dressings
US6243192B1 (en)	1997-04-28	2001-06-05	Timer Technologies, Llc	Electrochemical display and timing mechanism with migrating electrolyte
GB2324884A (en) *	1997-04-28	1998-11-04	Wisconsin Label Corp	Electrochemical display and timing mechanism with migrating electrolyte
US6331166B1 (en) *	1998-03-03	2001-12-18	Senorx, Inc.	Breast biopsy system and method
US6235396B1 (en)	1998-06-26	2001-05-22	Younger Mfg	Optical lens comprising a polyvinylalcohol layer covalently bonded to a bulk lens polymer
US6285492B1 (en)	1998-07-02	2001-09-04	Timer Technologies, Llc	Interactive electrochemical displays
DE69912793T2 (de) *	1998-07-31	2004-09-30	First Water Ltd., Marlborough	Bioadhäsive Zusammensetzungen und Biomedizinische Elektroden diese enthaltend
GB2341185A (en) *	1998-09-07	2000-03-08	Polybiomed Ltd	Polymerizable material and adhesive sheet material therefrom; dressings, electrodes and transdermal patches
GB9902238D0 (en) *	1999-02-02	1999-03-24	First Water Ltd	Bioadhesive compositions
US6878756B2 (en)	1999-02-02	2005-04-12	The Procter & Gamble Company	Disposable human waste management devices with improved adhesive flange attachment means to facilitate water adhesion stability with low pain level removal
US6544642B2 (en)	1999-02-02	2003-04-08	The Procter & Gamble Company	Disposable absorbent articles with improved adhesive for attachment to the skin to facilitate adhesion in oily conditions
US6607516B2 (en)	1999-02-02	2003-08-19	The Procter & Gamble Company	Disposable human waste management devices with improved adhesive flange to facilitate adhesion in oily conditions
US6710099B2 (en)	1999-02-02	2004-03-23	The Procter & Gamble Company	Disposable absorbent articles with improved adhesive for attachment to the skin to facilitate water adhesion stability with low pain level removal
GB9909349D0 (en) *	1999-04-23	1999-06-16	First Water Ltd	Process
US6297337B1 (en) *	1999-05-19	2001-10-02	Pmd Holdings Corp.	Bioadhesive polymer compositions
KR100452972B1 (ko) *	2000-05-16	2004-10-14	주식회사 삼양사	경피투여용 하이드로젤 조성물
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1995
- 1995-03-22 US US08/408,625 patent/US5614586A/en not_active Expired - Lifetime
- 1995-04-04 CA CA002146286A patent/CA2146286A1/fr not_active Abandoned
- 1995-04-05 EP EP95302283A patent/EP0676457B1/fr not_active Expired - Lifetime
- 1995-04-05 DE DE69505176T patent/DE69505176T2/de not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0676457A1 (fr)	1995-10-11
DE69505176T2 (de)	1999-06-10
EP0676457B1 (fr)	1998-10-07
US5614586A (en)	1997-03-25
DE69505176D1 (de)	1998-11-12

Legal Events

Date	Code	Title	Description
2001-04-04	FZDE	Discontinued

Publication	Publication Date	Title
US5614586A (en)	1997-03-25	Polyacrylate and Polymethacrylate ester based hydrogel adhesives
US5674275A (en)	1997-10-07	Polyacrylate and polymethacrylate ester based hydrogel adhesives
AU662582B2 (en)	1995-09-07	Biomedical electrode provided with two-phase composites conductive, pressure-sensitive adhesive
US5846558A (en)	1998-12-08	Ionically conductive adhesives prepared from zwitterionic materials and medical devices using such adhesives
US5354790A (en)	1994-10-11	Methods for the preparation of non-stringy adhesive hydrophilic gels
EP1100556B1 (fr)	2003-11-12	Compositions bioadhesives et electrodes biomedicales les contenant
JP4732644B2 (ja)	2011-07-27	ホットメルト特性を有する導電性感圧接着剤およびそれを用いた生体用電極
CA2588700C (fr)	2014-04-01	Procede pour la fabrication d'hydrogels adhesifs autocollants
US5985990A (en)	1999-11-16	Use of pendant free-radically polymerizable moieties with polar polymers to prepare hydrophilic pressure sensitive adhesive compositions
CN100553712C (zh)	2009-10-28	生物医学电极
JP4139123B2 (ja)	2008-08-27	ミクロエマルジョン組成物並びにその製造及び使用方法
EP1026219A1 (fr)	2000-08-09	Composition bioadhésive
KR20060117269A (ko)	2006-11-16	중합체 하이드로겔 조성물
WO1997024378A1 (fr)	1997-07-10	Utilisation de fragments pendants a polymerisation radicalaire ainsi que de polymeres polaires en vue de la preparation de compositions adhesives hydrophiles et sensibles a la pression
WO1997024376A1 (fr)	1997-07-10	Utilisation de fragments photosensibles pendants sur des precurseurs de polymeres en vue de la preparation d'adhesifs hydrophiles sensibles a la pression